Paying Medical Bills, Making Hospital Visits & More of the Nicest Things Taylor Swift Has Ever Done for Her Fans

On March 25, 2020, the "Lover" singer donated to several fans who publicly expressed their financial struggles during the COVID-19 health crisis. One of them was Samantha Jacobson, who received a $3,000 donation after writing on her Tumblr that she has "no job, no income, no way to pay my bills" after her workplace shut down over coronavirus concerns.

"I was in shock," Jacobson - a 24-year-old cocktail server at a bar in Disney Springs in Orlando, Florida - tells PEOPLE of Swift's surprise donation. "I was just speechless. I couldn't believe someone I had looked up to and love and respected for so long has reached out with such generosity."

According to Jacobson, Swift reached out to her on Twitter and offered to help alleviate some of her financial burdens.

The superstar surprised one of her teen fans who is battling stage four cancer when she donated $10,000 toward her medical bills in September 2019.

Just 16 years old, Trinity Foster was diagnosed with stage four osteosarcoma, and created a GoFundMe page to help with her bills. She caught the attention of Swift when she held an album release party for her latest album, Lover. 

The Grammy winner left a sweet note Trinity's GoFundMe page, along with her donation: "Trinity, I saw photos of your album release party that you did in your hospital room and wanted to say thank you for being so kind and supportive! I hope I can give you a hug in person soon, but in the meantime I wanted to send you this and all my love. Your friend, Taylor." 

In August 2019, Swift sent a Toronto-based student, Ayesha Khurram, $6,386.47 CAD - which converts to about $4,800 USD - to help pay for her tuition. The Swiftie posted to Instagram in complete shock writing, "I posted about struggling with paying for tuition. Two hours later, I get [a receipt] in my email. I have no words and I can't stop crying. I don't have words." 

Taylor's message to her grateful fan? "Ayesha, get your learn on girl. I love you! Taylor."

In October 2018, the Grammy winner (pictured here with her own mom) quietly donated $15,500 to a young fan struggling with the pressures of providing for her family.

"My Mom has been in a coma for three years now. She had an ulcer that bled out that led to lack of oxygen to the brain which resulted in brain damage," 19-year-old Sadie wrote in a heartbreaking note posted to her Twitter account. "We take care of her at home full time. My dad is unable to work because he has to always be with my Mom. My older brother and I have to provide for our family," continued the full-time college student. "My family is in trouble."

Acknowledging she has reached her "breaking point," Sadie revealed her mom, Lauriann Bartell, fell into a coma two days before she saw the 1989 tour. "I'm grateful to Taylor for keeping me afloat through it all," she wrote.

Swift donated money via the family's GoFundMe page, simply signing the donation "Love, Taylor, Meredith and Olivia Swift." With Swift's generous gesture, more than $25,000 has now been raised for Sadie's family.

In 2016, Swift donated $10,000 to help Jacob Hill, who has autism, purchase a service dog. Two years later, she met the boy, his family - and the pup! 

Swift hosted Hill backstage at her September 2018 NRG Stadium show in Houston. The young fan and his service dog, Reid, shared the special moment with his mother, Allison Hill and sister, Jordan Fox.

"Taylor Swift was so kind. She said Reid was a big puffball and so cute. She was especially awesome with Jacob. She didn't see my son's disability she just saw him," Allison shared in a Facebook post for Autism Speaks. "She got on her knees and looked him right in the eyes and said hello and she was thankful HE came to her show even though she knew it was loud and there was so much going on."

Swift and Meghan McCain teamed up to make one special fan's dream come true!

Twenty-one-year-old Lexi Caviston's dream turned into reality when the Philadelphia native was able to meet the pop star at her Lincoln Financial Field show in July 2018.

The meeting was made possible after McCain came across a tweet that Caviston's best friend, Alexandra, wrote as part of the social media campaign #LexiStrong. "My best friend Lexi was diagnosed with brain cancer (glioblastoma) in December. We're going to the #reputationstadiumtour on July 14th in Philly and it's her dream to meet @taylorswift," the tweet read.

"She has the same brain cancer my dad does," McCain explained during an episode of The View.

"I am so happy that we were able to help Lexi forget about her cancer for one day," she continued. "She spoke to our producer and said it was by far the best day of her life."

Isabella McCune couldn't leave the hospital to see Swift in concert, so Swift came to see her instead.

The Grammy winner paid it forward in May 2018, taking a break from her Reputation Stadium Tour rehearsals in Glendale, Arizona, to surprise McCune, an 8-year-old fan who found strength in Swift's music after she was severely burned in a fire pit explosion on St. Patrick's Day.

"Taylor took time out of her busy, busy schedule and sat down on the bed next to Isabella," her mother, Lilly McCune, told PEOPLE on the phone from the Arizona Burn Center at Maricopa Medical Center in Phoenix. "She brought her a bag with goodies from her tour. She said she had to meet her because she was so inspired by her story and honored that her music helped her."

"When she was leaving, my daughter asked for a hug and Taylor turned around and said, 'Absolutely - I didn't want to hurt you,'" said Lilly, who added that Swift's parents joined in on the visit, too. "They hugged and it was so heartfelt. I knew it meant a lot to Isabella."

The "Delicate" singer met her "littlest fans" - foster children from Arizona - in May 2018 when she invited more than 2000 special guests to her final dress rehearsal of her upcoming Reputation Stadium Tour.

An attendee tells PEOPLE Swift spoke to the crowd of excited children and foster parents before the show and asked if it was their first time attending a concert. About 500 hands flew into the air, the concertgoer says.

Abbi Williams, a foster mother, shared photos of the experience on Instagram, including photos of her children alongside her friend's foster children smiling in a group photo with Swift, as well as holding up autographed covers of Reputation.

Another mother, going by the name Momma Bear on Instagram, also shared photos of her foster children, writing, "When @taylorswift invites you to her final dress rehearsal, you go. We couldn't bring cameras in, just know that if you are able to see her #reputationstadiumtour DO IT! She was such a gracious and generous hostess…complete with a pizza party and photo op afterward.

Swift made another young fan's dreams come true in May 2018.

The month prior, 13-year-old Cora - who had been looking forward to attending the singer's upcoming tour stop at CenturyLink Field in Seattle for months - was diagnosed with Hodgkin's lymphoma, according to local station KING 5 News.

Though Cora was devastated after her doctors advised her to stay away from large crowds, the teen's best friend Katherine hatched a plan to get her safely to the show.

The local fire station got wind of the teens' story after Katherine reached out to KING 5, and the station's captain Jeff Bellinghausen offered his firefighters to drive Cora and Katherine to the stadium, according to the news station.

Surprised by a waiting ambulance on the day of the concert, Cora and Katherine were driven to a private entrance and even got to meet Swift before the superstar hit the stage.

"I didn't think I was going to get to go to this concert because of all the people and all of the potential germs, and Katherine made it happen," Cora told KING 5.

The "End Game" singer gave two of her biggest fans the surprise of a lifetime in January 2018, when she sent them flowers and a personalized note to celebrate their wedding day.

Gonzales, who also goes by Lexi, and Lewis tied the knot in a sweet ceremony and reception at Noah's Event Venue in Dickinson, Texas after over 9 years together. They began dating in high school, when Swift's 2008 tune "Love Story" became an integral part of their own love story. Lewis even quoted lyrics from the song when she proposed in November of 2016.

"Lexi & Brittany, you have no idea how honored I am that 'Love Story' has been such a big part of your beautiful love story," Swift wrote in her note - photos of which Gonzales shared to Twitter. "I'm absolutely thrilled that Lexi said YES! Have the most magical wedding day and hopefully I can meet you both soon! Love, Taylor."

Sharing her story on the Grammy winner's The Swift Life app in December 2017, a fan named Stephanie prefaced her post by saying she had contemplated whether or not to post about her experience.

"I've finally decided to tell you all what Taylor did for me this night," wrote Stephanie, who accompanied her post with photos of herself backstage with Swift at her 1989 tour, her house and baby girl. "What many of you don't know is that for eight months of my pregnancy I was homeless."

"Long story short our first flat was condemned for health and safety reasons and we lost everything. To add to the stress, during this time [my partner] Matthew lost his job."

While attending Swift's concert in Manchester, Stephanie says her mother filled in the "End Game" singer about her daughter's difficult situation and simply asked the star to make her "feel special" that night.

"After the show Taylor took us back to her dressing room where she told me, 'Stephanie, You've been in my life for a long time and you've never asked me for anything. You could have reached out and I would have helped you. But you didn't. [Your] mum told me.."

Swift told Stephanie she was going to give her money for her concert ticket but ended up helping "us buy a home and all I needed for my baby," she continued.

The "Look What You Made Me Do" singer took a U.K. fan named Lara by surprise when she joined her live stream, which was recorded by a friend, in October 2017.

Lara expressed her gratitude to Swift, crying through tears to say: "I have to say thank you for everything, you've actually made my life so much better."

In a second post uploaded days later, Lara revealed that Swift had personally visited her, along with her boyfriend Joe Alwyn's younger brother Patrick.

"On Thursday last week Taylor Nation DM'd me," she said. "They said Taylor would be sending me a package. I'm so grateful for Taylor Alison Swift."

But of course she did far more than just send a gift. Swift personally delivered the package herself.

The singer gave her young fan T-shirts and sweatshirts from her Reputationline. Swift's boyfriend lives in England, so she may be in town visiting Alwyn.

Just when you thought that Swift couldn't possibly top her 1989 Secret Sessions, she went and surprised 100 lucky U.K.-based fans when she invited them over on Friday the 13th (always with the 13!) in 2017 to listen to Reputation. The best part? Those lucky fans also got to pose for photos with Olivia Benson herself.

The Swift fans at the office of Craftsy, a Denver crafting website, were gifted a bunch of bright bouquets from the singer following her sexual assault trial in August 2017. During the trial, Craftsy's staff publicly supported Swift by arranging Post-It notes in their office windows reflecting Swift's own lyrics back at her in a show of solidarity. "Supporting creative individuals is what we're all about," read the company's Instagram, captioning more than a handful of bouquets. "@taylorswift we're glad that our window messages brightened your days in Denver just as the flowers you sent are brightening ours!"

In April 2019, a fan named Lindsay shared on Twitter that the Grammy winner had sent her a floral arrangement and handwritten note.

In an emotional video, Lindsay - who was hospitalized following a frightening car accident - broke down crying as her loved ones help her open the note that was sent on Swift's personal stationery.

"i finally stopped crying long enough to post that taylor swift just sent me flowers and a handwritten note… im still in complete utter shock," Lindsay wrote on Twitter. "i love you endlessly, you have NO IDEA how much this meant to me."

Swift sent her well wishes in May 2017 after a fan invited the star to her graduation party.

"I INVITED TAYLOR TO MY GRADUATION PARTY AND SHE SENT ME FLOWERS AND THIS CARD 😭😭😭 I LOVE YOU HONEY @taylorswift13," the fan - who has seen Swift in concert eight times - tweeted, along with photos of the flowers and hand-written note by the singer.

The singer's message was personally addressed, starting off, "Ashley, Hi love! I'm so sad that I can't make it to your graduation party! The New York theme, the photo booth, it being on the 13th…that's my kinda party."

She applauded the graduate, continuing, "I'm so proud of you, your hard work and dedication, your excitement and ambition. I'm very lucky that a girl like you cares about me."

The Monday after Christmas 2016, the "Shake It Off" singer showed up at the Missouri home of the world's "Oldest Swifty": a 96-year-old World War II veteran who says that his love for Swift has brought him closer to his 20-plus grandchildren. A little after 1 p.m., Swift appeared and surprised him and his family with an impromptu performance and celebration. 

Longtime Swift fan Max Singer got the surprise of his life when the singer "crashed" his 2016 wedding to treat him and his new wife, Kenya Smith, to a stripped-down performance of "Blank Space." Singer's sister, Ali, had reached out to Swift to tell her about the death of the siblings' mother, and how Singer and Smith had wed in the hospital so that she could be there for her son's big day - and how they danced to "Blank Space" as their mother-son dance. If her surprise performance wasn't sweet enough, Swift also gifted the newlyweds with a handmade, hand-painted card, because she's just that kind.

When 12-year-old Australian fan Jorja Hope was diagnosed with progressive hearing loss that will eventually cause her to go deaf, the first thing she said was, "I won't be able to hear Taylor Swift," reports The Maitland Mercury. But Swift made sure Jorja had the chance to make precious musical memories before that time comes. After Jorja's twin sister Chloe launched a Facebook campaign to help Jorja meet her idol at Swift's November tour stop in Sydney, radio station Nova 96.9 helped set up a meeting with the superstar, who of course happily accepted. The singer "gave Jorja a massive hug," and the fan told Maitland Mercury "she was very, very amazing."

There's only one thing better than watching Dylan, a 7-year-old Swiftie, adorably break it down to "Shake It Off" - and that's watching him break it down with Taylor Swift herself. After seeing the internet sensation bust a move online and on The Ellen DeGeneres Show, Swift met up with Dylan for the cutest dance party ever.

When Emily Beazley picked up the phone on April 28, 2015, there was a very familiar voice on the line. After friends and family campaigned on social media, Taylor Swift called the 12-year-old - who has been battling stage III T-cell lymphoblastic Non-Hodgkin's lymphoma since 2011 - to say how much it meant to her that her music helped the young fan get through painful treatments.

Swift took #SquadGoals to a new level at the 2015 iHeartRadio Music Awards, where she tracked down two of her biggest fans (sound familiar?) for a pre-show hang. "Taylor talked to me like she was my best friend," Colleen Sullivan, one of the lucky chosen ones, told BuzzFeed. "She's so welcoming, and she really wants to thank us for supporting her all these years. It's amazing how I can play a part in her happiness when she's always played a huge role in mine."

Jalene Salinas made a bucket list: In addition to things like building a snowman and going to a spa, the 4-year-old diagnosed with a PNET tumor dreamed of dancing with Swift to "Shake It Off." #ShakeItOffJalene caught the singer's eye, and she met her young fan during a March 2 FaceTime chat. "I'm so happy to talk to you," Swift told Jalene during their 20-minute catchup, just weeks before Jalene passed away. "And I'm so happy you like 'Shake It Off.'"

Sam Smith, you can keep your trophies - we'd rather leave the Grammys with swelfies (sorry, we couldn't resist). The true winner of the night at the 2015 Grammys was Jill, whom Swift reached out to on Tumblr after learning her die-hard fan was also attending music's biggest night. Jill chronicled their backstage hang on Tumblr, even confirming that Swift had something in common with us less-photogenic mortals: "We took our pictures, and after we took the one of her putting her arm around me, she said, 'Let's take another. I look creepy.'"

We can officially confirm Swift had the cutest Valentine's Day date in 2015: Tumblr superfan Sophie, who headed to Swift's envy-inducing N.Y.C. apartment for an afternoon of baking, flower crowns and cats. It's just one way the happily single Swift is focusing on the true loves of her life: you know, her fans and her cats.

Ice cream only goes so far when you're heartbroken, which is why Kasey reached out to someone who knows a few things about getting through breakups. Swift replied to the teenage fan's Tumblr post with a playlist and some solid advice for your Pinterest quote board: "There is nothing wrong with avoiding people who hurt you."

Even Ebenezer Scrooge could appreciate Swift's seasonal cheer, which resulted in a new holiday just for her fans: Swiftmas. The lucky ones on her nice list in 2014 were treated to presents hand-picked by Swift, which is, like, a thousand times better than the socks your aunt gave you for Christmas.

Over Christmas in 2014, Swift superfan Stephanie Barnett's toddler son got a pint-size Mercedes - but the delivery person was the real present. Swift showed up at their Connecticut home, which left Barnett "literally bawling on my couch. Like inconsolably, that she would do this for me and my son."

But unlike Santa Claus, you never know when Swift is comin' to town (also: cats > reindeer). Case in point: A Swiftie named Rebekah received a package from her idol in January 2015 containing a handwritten letter, Polaroids, assorted presents and a check for (drum roll) $1,989.

Like all brides-to-be, Gena Gabrielle's wedding registry wasn't complete without one very essential item: Sorry, blenders - we're talking about a shower cameo from Swift. The singer headed to Columbus, Ohio, to surprise her fan with kitchen goods, a cookbook and a supply of selfies that deserve inclusion in her wedding album.

As any self-respecting Swift fan has noticed, the singer likes to keep an eye on her fans' social accounts - they don't call it Taylurking for nothing. But there's no hashtag to properly summarize how much excitement a handful of fans around the world felt when they were invited to listen to her new album at super-exclusive listening parties, dubbed #1989SecretSessions.

During Swift's trip to Australia, she surprised patients at Lady Cilento Children's Hospital in Brisbane, dropping by to take photos. One fan (who has a lyrical pillow we are all sorts of jealous of) had a selfie photo shoot with Swift, who told her, "Now you have to take it because I'm going kiss you on the cheek." Aww! The hospital posted on its Facebook page, "Thank you Taylor Swift for dropping by the Lady Cilento Children's Hospital this afternoon to give our patients and families a special surprise they'll never forget. They'll never 'shake off' the memories you made tonight."